Flotilla Holidays Sailing Vacations

Offshore Sailing School encourages everyone who loves to sail, especially those who have earned US Sailing Bareboat Cruising Certification, to purchase a cabin as a single or couple and join these hosted sailing trips.

The boats we charter in the Caribbean and fabulous cruising grounds in Mediterranean waters, are usually 42′-50′ catamarans and monohulls. You are assigned to sail with like-minded adventurers by the cruise leaders, bearing in mind that a certain level of physical ability and the desire to participate in handling the boat is a must. Check out our Flotilla Cruising FAQs, and note these points below:

Colgate Sailing Adventures® Flotilla Cruises are led and hosted by Heather and Nate Atwater, or Daniel and Klaudia Jackson, or other Offshore Sailing School instructor teams.

Flotilla cruise leaders and sometimes participants write a blog during each cruise providing interesting recaps of these great adventures. WindCheck magazine has run several stories written by Heather in reports on the 2020 trip in the Apostle Islands of Lake Superior, 2019 trip in Croatia, and an earlier story from 2018. If you haven’t participated in one of the best sailing vacations you’ll find, why not now? Register for one of our sailing holidays today!

Flotilla sailboat vacations provide lasting friendships and take you to places you might never go on your own. Colgate Sailing Adventures® flotilla sailing holidays are open to all sailors with sailing certifications or requisite experience. They sell out fast!

It is very important that anyone who wants to skipper or be an official mate on a Colgate Sailing Adventures® flotilla cruise, hold US Sailing Bareboat Cruising Certification provided by Offshore Sailing School, and carry an International Proficiency Certificate (IPC). The IPC is a Certificate which will certify you to bareboat charter in countries overseas. Discounts are available that recognize these levels. Please see each cruise for more details.

To find the best flights from your home base to Colgate Sailing Adventures® destinations, we recommend you contact flights@thlmarine.com or Moorings/Sunsail travel service (866-649-2003).

Colgate Sailing Adventures® flotilla sailboat vacations are the best way to enjoy bareboat chartering – you sail the boat, and Offshore Sailing School takes care of all the details. Sign up, pack your sailing clothes, and meet at the cruise departure location for these turn-key sailing holidays.

With private cabins, spacious main salons, cockpits and decks, these boats are ideal for socializing and enjoying the outdoors. Purchase a single private cabin, or share a cabin with a spouse or sailing partner. Individuals and couples are assigned to each boat based on sailing resumes required from everyone on the cruise.

Everyone shares the fun, steering, trimming sails and visiting fantastic locations on the best sailing holidays you’ll find. In the evenings, stories and laughter abound as you relax under a canopy of stars while dining al fresco in the cockpit or at a quayside restaurant. Each morning your Cruise Leaders make the rounds to discuss the itinerary and navigation. On a Colgate Sailing Adventures® flotilla cruise, all the boats follow the same route each day and rendezvous in an anchorage or harbor each night.

Colgate Sailing Adventures® flotilla cruise sailboat vacations are for sailors who enjoy the company of other sailors. Each boat must have two bareboat cruising certified sailors aboard (the designated skipper and mate). Experienced sailors and those with minimum certification at the Learn to Sail level on boats of at least 26’ in length are welcome too. The minimum age for participation is 18. Contact an Offshore Sailing School representative today.